Absolute Configuration Determination for Natural Products (I)

被引：0

作者：

Shen Lan ^{[1
,2
]}

Zhao Sheng-Ding ^{[1
]}

Zhu Hua-Jie ^{[1
]}

机构：

[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Organ Synth & Nat Prod Lab, Kunming 650204, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2011年 / 32卷 / 11期

关键词：

Natural product; Density functional theory; Optical rotation; C-13 NMR computation; Absolute configuration determination; CIRCULAR-DICHROISM SPECTROSCOPY; FUNCTIONAL THEORY CALCULATION; AB-INITIO CALCULATION; OPTICAL-ROTATION; MOLECULAR-STRUCTURE; NMR; METABOLITES; ASSIGNMENT; SPECTRA; SHIFTS;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optical :rotation and C-13 NMR computations for five natural products, vidalenolone(1), 2-(3-di-hydroxy-3 -methylbutyl) benzene-1,4 -diol (2), 5, 6, 7, 7a (S)-tetrahydro-2-hydroxy-1-(p-hydroxyphenyl)-3H-pyrolizin -3-one (3), 3, 4-dihydro-4, 8-dihydroxy-6-methoxy-7-methyl-1 (2H)-naphthalenone (4) and 6-(R)-(4'-oxopentyl)-5,6-dihydro-2H-pyran-2-one(5), were performed at the B3LYP/6-aug-cc-pVDZI/B3LYP/6-31G(d) levels for assigning their absolute configurations. The computational results matched the experimental results well. One compound's 13C NMR chemical shifts were corrected based on the computational C-13 NMR results and earliest reports.

引用

页码：2568 / 2573

页数：6

共 43 条

[1] New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp.
Abdel-Lateff, A
König, GM
Fisch, KM
Höller, U
Jones, PG
Wright, AD
[J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11): : 1605 - 1611
[2] Barone G, 2002, CHEM-EUR J, V8, P3233, DOI 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO
[3] 2-0
[4] NMR and calculational studies on the regioselective lithiation of 1-methoxynaphthalene
Betz, J
Bauer, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) : 8699 - 8706
[5] Quantum mechanical calculations of NMR J coupling values in the determination of relative configuration in organic compounds
Bifulco, G
Bassarello, C
Riccio, R
Gomez-Paloma, L
[J]. ORGANIC LETTERS, 2004, 6 (06) : 1025 - 1028
[6] Ab initio calculation of optical rotation in (P)-(+)-[4]triangulane
Crawford, TD
Owens, LS
Tam, MC
Schreiner, PR
Koch, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) : 1368 - 1369
[7] Ab initio calculation of molecular chiroptical properties
Crawford, TD
[J]. THEORETICAL CHEMISTRY ACCOUNTS, 2006, 115 (04) : 227 - 245
[8] Della Monica C., 2002, TETRAHEDRON LETT, V43, P5707
[9] Artarborol, a nor-caryophyllane sesquiterpene alcohol from Artemisia arborescens. stereostructure assignment through concurrence of NMR data and computational analysis
Fattorusso, Caterina
Stendardo, Emiliano
Appendino, Giovanni
Fattorusso, Ernesto
Luciano, Paolo
Romano, Adriana
Taglialatela-Scafati, Orazio
[J]. ORGANIC LETTERS, 2007, 9 (12) : 2377 - 2380
[10] Frisch J., 2003, Gaussian 03

← 1 2 3 4 5 →